Synthesis of oxazino[4,3-a]indoles by domino addition-cyclization reactions of (1H-indol-2-yl)methanols and vinyl selenones in the presence of 18-crown-6

被引：12
作者：
Palomba, Martina [1 ]
Vinti, Elisa [1 ]
Marini, Francesca [1 ]
Santi, Claudio [1 ]
Bagnoli, Luana [1 ]
机构：
[1] Univ Perugia, Grp Catalysis & Organ Green Chem, Dept Pharmaceut Sci, Via Liceo 1, I-06123 Perugia, Italy
来源：
TETRAHEDRON | 2016年 / 72卷 / 44期
关键词：
Vinyl selenones; Domino reactions; (1H-Indol-2-yl)methanols; Oxazino[4,3-a]indoles; ONE-POT SYNTHESIS; MICHAEL REACTION; N-ALKYLATION; INDOLES; STRATEGY; PYRROLE; ESTERS; ROUTE;
D O I：
10.1016/j.tet.2016.09.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein we report the synthesis of biologically relevant oxazino[4,3-a]indoles by an environmentally friendly Michael addition-cyclization cascade using potassium hydroxide in dichloromethane employing variously substituted vinyl selenones and (1H-indol-2yl)methanols. The addition of 18-crown-6, as a complexing agent, is crucial to achieve high chemo- and regio-selectivity. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7059 / 7064
页数：6
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